DE2627910C2 - 16-phenoxy- und 16-substituierte phenoxyprostatriensaeurederivate und verfahren zu ihrer herstellung - Google Patents

16-phenoxy- und 16-substituierte phenoxyprostatriensaeurederivate und verfahren zu ihrer herstellung

Info

Publication number: DE2627910C2
Authority: DE; Germany
Prior art keywords: compound; phenoxy; formula; acid; pgf
Prior art date: 1975-06-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

DE2627910A

Other languages

German (de)

English (en)

Other versions

DE2627910A1 (de

Inventor

John H. Palo Alto Calif. Fried

Joseph M. Mexiko / México Muchowski

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Syntex USA LLC

Original Assignee

Syntex USA LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-06-23

Filing date

1976-06-22

Publication date

1985-01-17

1976-06-22 Application filed by Syntex USA LLC filed Critical Syntex USA LLC

1977-01-13 Publication of DE2627910A1 publication Critical patent/DE2627910A1/de

1985-01-17 Application granted granted Critical

1985-01-17 Publication of DE2627910C2 publication Critical patent/DE2627910C2/de

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims description 13
238000000034 method Methods 0.000 title claims description 12
238000004519 manufacturing process Methods 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 41
150000004702 methyl esters Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 3
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
241001465754 Metazoa Species 0.000 description 11
150000003180 prostaglandins Chemical class 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
239000000203 mixture Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229940094443 oxytocics prostaglandins Drugs 0.000 description 6
239000002904 solvent Substances 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
230000035935 pregnancy Effects 0.000 description 5
231100000176 abortion Toxicity 0.000 description 4
206010000210 abortion Diseases 0.000 description 4
-1 hydroxy fatty acids Chemical class 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000012360 testing method Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
241000699800 Cricetinae Species 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
238000010306 acid treatment Methods 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
229940124630 bronchodilator Drugs 0.000 description 2
239000006172 buffering agent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
210000003754 fetus Anatomy 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000012907 medicinal substance Substances 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
229930014626 natural product Natural products 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000003791 organic solvent mixture Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
JYDHZOIDIWUHDB-UHFFFAOYSA-N 1-(4-phenylpiperidin-4-yl)ethanone;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(C(=O)C)CCNCC1 JYDHZOIDIWUHDB-UHFFFAOYSA-N 0.000 description 1
NQTSTBMCCAVWOS-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-phenoxypropan-2-one Chemical compound COP(=O)(OC)CC(=O)COC1=CC=CC=C1 NQTSTBMCCAVWOS-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000699673 Mesocricetus auratus Species 0.000 description 1
208000037656 Respiratory Sounds Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000282887 Suidae Species 0.000 description 1
VSOIOGROSODCFE-UHFFFAOYSA-N [Cu].[Li]C Chemical compound [Cu].[Li]C VSOIOGROSODCFE-UHFFFAOYSA-N 0.000 description 1
HRNSPWKFRJGQEC-UHFFFAOYSA-N [Cu]C Chemical compound [Cu]C HRNSPWKFRJGQEC-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000003509 anti-fertility effect Effects 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
241001233037 catfish Species 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000013329 compounding Methods 0.000 description 1
210000004246 corpus luteum Anatomy 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000003001 depressive effect Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000007865 diluting Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
230000012173 estrus Effects 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
150000002373 hemiacetals Chemical class 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
210000004914 menses Anatomy 0.000 description 1
231100000551 menstrual abnormality Toxicity 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000016087 ovulation Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000006179 pH buffering agent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
MLBYLEUJXUBIJJ-UHFFFAOYSA-N pent-4-ynoic acid Chemical compound OC(=O)CCC#C MLBYLEUJXUBIJJ-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 1
239000006187 pill Substances 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
230000036515 potency Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000002997 prostaglandinlike Effects 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
238000000746 purification Methods 0.000 description 1
206010037833 rales Diseases 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
UPDATVKGFTVGQJ-UHFFFAOYSA-N sodium;azane Chemical compound N.[Na+] UPDATVKGFTVGQJ-UHFFFAOYSA-N 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DE2627910A 1975-06-23 1976-06-22 16-phenoxy- und 16-substituierte phenoxyprostatriensaeurederivate und verfahren zu ihrer herstellung Expired DE2627910C2 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US58921875A	1975-06-23	1975-06-23
US05/643,219 US3985791A (en)	1975-06-23	1975-12-22	16-Phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives

Publications (2)

Publication Number	Publication Date
DE2627910A1 DE2627910A1 (de)	1977-01-13
DE2627910C2 true DE2627910C2 (de)	1985-01-17

Family

ID=27080476

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE2627910A Expired DE2627910C2 (de)	1975-06-23	1976-06-22	16-phenoxy- und 16-substituierte phenoxyprostatriensaeurederivate und verfahren zu ihrer herstellung

Country Status (13)

Country	Link
US (1)	US3985791A (es)
AU (1)	AU505899B2 (es)
CA (1)	CA1064027A (es)
DE (1)	DE2627910C2 (es)
ES (1)	ES449162A1 (es)
FR (1)	FR2315263B1 (es)
GB (1)	GB1546823A (es)
HK (1)	HK8780A (es)
IE (1)	IE43916B1 (es)
MX (1)	MX3949E (es)
MY (1)	MY8000274A (es)
NL (1)	NL181628C (es)
SE (2)	SE417710B (es)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4178457A (en) *	1978-07-10	1979-12-11	Syntex (U.S.A.) Inc.	(dl)-16-Phenoxy- and 16-substituted phenoxy-9-keto prostatrienoic acid derivatives and processes for the production thereof
US4389414A (en) *	1981-05-11	1983-06-21	Syntex (U.S.A.) Inc.	Prostaglandin compositions
US4804787A (en) *	1983-12-22	1989-02-14	Syntex (U.S.A.) Inc.	Processes and intermediates for making 16-phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives
US4912235A (en) *	1983-12-22	1990-03-27	Syntex (U.S.A.) Inc.	Processes and intermediates for making 16-phenoxy- and 16-substituted phenoxy-prostatrienoic acid derivatives and their stereoisomers
DE3414509A1 (de) *	1984-04-13	1985-10-24	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue 9-halogen-prostaglandine
FI853907L (fi) *	1984-10-09	1986-04-10	Syntex Inc	Mellanprodukter foer framstaellning av 16-fenoxi- och 16-substituerade fenoxi-prostatriensyraderivat.
US4778904A (en) *	1985-09-13	1988-10-18	Syntex (U.S.A.) Inc.	Intermediates for making 16-phenoxy- and 16-(substituted phenoxy)-prostatrienoic acid derivatives
US4929740A (en) *	1984-10-09	1990-05-29	Syntex (U.S.A.) Inc.	Process for making 16-phenoxy- and 16-(substituted phenoxy)-prostatrienoic acid derivatives
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1975
- 1975-06-23 ES ES449162A patent/ES449162A1/es not_active Expired
- 1975-12-22 US US05/643,219 patent/US3985791A/en not_active Expired - Lifetime
1976
- 1976-06-09 MX MX76286U patent/MX3949E/es unknown
- 1976-06-17 GB GB25203/76A patent/GB1546823A/en not_active Expired
- 1976-06-17 CA CA255,145A patent/CA1064027A/en not_active Expired
- 1976-06-18 IE IE1329/76A patent/IE43916B1/en unknown
- 1976-06-21 NL NLAANVRAGE7606723,A patent/NL181628C/xx not_active IP Right Cessation
- 1976-06-21 AU AU15079/76A patent/AU505899B2/en not_active Expired
- 1976-06-21 SE SE7607075A patent/SE417710B/xx not_active IP Right Cessation
- 1976-06-21 FR FR7618857A patent/FR2315263B1/fr not_active Expired
- 1976-06-22 DE DE2627910A patent/DE2627910C2/de not_active Expired
1980
- 1980-03-06 HK HK87/80A patent/HK8780A/xx unknown
- 1980-11-27 SE SE8008334A patent/SE424636B/sv not_active IP Right Cessation
- 1980-12-30 MY MY274/80A patent/MY8000274A/xx unknown

Also Published As

Publication number	Publication date
SE417710B (sv)	1981-04-06
AU1507976A (en)	1978-01-05
DE2627910A1 (de)	1977-01-13
IE43916L (en)	1976-12-23
CA1064027A (en)	1979-10-09
HK8780A (en)	1980-03-14
SE7607075L (sv)	1976-12-24
FR2315263B1 (fr)	1978-11-10
AU505899B2 (en)	1979-12-06
MX3949E (es)	1981-10-09
SE8008334L (sv)	1980-11-27
FR2315263A1 (fr)	1977-01-21
US3985791A (en)	1976-10-12
NL181628C (nl)	1987-10-01
IE43916B1 (en)	1981-07-01
ES449162A1 (es)	1977-12-16
MY8000274A (en)	1980-12-31
GB1546823A (en)	1979-05-31
NL7606723A (nl)	1976-12-27
SE424636B (sv)	1982-08-02

Legal Events

Date	Code	Title
1982-04-29	8110	Request for examination paragraph 44
1985-01-17	D2	Grant after examination
1985-07-11	8364	No opposition during term of opposition
1994-06-09	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
DE2627910C2 (de)	1985-01-17	16-phenoxy- und 16-substituierte phenoxyprostatriensaeurederivate und verfahren zu ihrer herstellung
DE69716226T2 (de)	2003-06-05	Difluoroprostaglandin-Derivate und ihre Anwendung
DE2927715C2 (es)	1987-08-27
DE2731868C2 (es)	1987-06-04
DE2437388A1 (de)	1975-02-13	Prostansaeurederivate
DE2154309C3 (de)	1981-06-19	17-Phenyl-18,19,20-trinor-PGE↓2↓ und - PGF↓2↓ α und dieselben enthaltende Arzneimittel
DE2355540C2 (de)	1982-11-18	16-Phenoxy-&omega;-tetranorprostaglandinderivate
DE2242239A1 (de)	1973-03-22	Neue 2-descarboxy-2- eckige klammer auf tetrazol-5-yl eckige klammer zu prostaglandine, verfahren zu ihrer herstellung sowie zwischenprodukte
DE1801750C3 (de)	1981-02-12	Prostaglandin-E-Carbinole und deren Tricarbonsäureester
DE2524326A1 (de)	1975-12-11	11-deoxy-13-dihydroprostaglandin-9- ketale
EP0099538B1 (de)	1991-09-11	Neue Carbacycline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE2626888A1 (de)	1977-04-07	11-desoxy-16-aryloxy-omega-tetranorprostaglandine
DE2346706A1 (de)	1975-04-03	Neue, nicht natuerlich vorkommende analoga von prostansaeuren und verfahren zu ihrer herstellung
CH617187A5 (es)	1980-05-14
DE2746932A1 (de)	1978-11-02	5,9-cyclische aether von 9-deoxy- prostaglandin-f tief 1alpha -artigen verbindungen und verfahren zu deren herstellung
CH640847A5 (en)	1984-01-31	Process for preparing analogues of 5,6-dihydroprostacyclin
DE2550004A1 (de)	1977-05-18	Thiaprostaglandine
DE2647969A1 (de)	1977-05-05	Cyclische amide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
DE2628364A1 (de)	1977-01-13	Dl- und 8r-9-fluorprostadiensaeurederivate und verfahren zu deren herstellung
DE2709347A1 (de)	1977-09-15	Erythro-15,16-dioxyprostensaeuren und -ester sowie verfahren zu ihrer herstellung
DE2513371C2 (de)	1982-07-15	9,11,15-Trihydroxy-13-thia-5-prostensäure-Derivate und diese enthaltende pharmazeutische Zubereitungen
DE2603172A1 (de)	1976-08-05	Prostaglandinantagonisten, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
EP0043446B1 (de)	1984-02-22	Neue 13-Thiaprostaglandin-Zwischenprodukte, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von 13-Thiaprostaglandin-Derivaten
DE2715921A1 (de)	1977-10-27	Neue zwischenprodukte und verfahren zur herstellung von thromboxan b tief 2
DE2621576A1 (de)	1976-12-02	3,5-bisoxydierte-2-(omega-halogen- 3-oxydierte-1-alkenyl)-cyclopentan-1- oenanthsaeuren und deren derivate, die herstellung dieser verbindungen sowie diese verbindungen enthaltende praeparate